On the apparent ketonization of the [MC2H4]+ ion from o‐hydroxybutyrophenone

Molenaar-Langeveld, T. A.; Nibbering, Nico M. M.; Morgan, R.P.; Beynon, J. H.

doi:10.1002/oms.1210130311

Cited by 12 publications

(9 citation statements)

References 16 publications

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“…Helium, H 2 , and 02 (Matheson), CH 30H (Aldrich), and CD 30D, CD 3CN, and c"HsCN (Merck) were obtained commercially and were used without further purification. Carbon-13-labeled benzonitrile la was available from a previous study [8]. The D-labeled benzonitriles Ib-le were obtained by dehydration [9] of the corresponding benzamides, which were available from an earlier study [10].…”

Section: Methodsmentioning

confidence: 99%

Site of protonation of benzonitrile hydrogen interchange in the protonated species

Wincel

Fokkens

Nibbering

1990

J. Am. Soc. Mass Spectrom.

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The site of protonation of gaseous benzonitrile in reactions with Ht, CH 30Hi, and CH 3CNH+ as protonating agents has been examined by using tandem mass spectrometry in combination with deuterium and 13C labeling. Metastable and collision-induced dissociation studies of CoXsCNX+ (X = H or D) show that proton attachment occurs on the CN group. The metastably decomposing Cj;XsCNX+ leads only to Cj;Xs + + XCN. This reaction proceeds via a mechanism involving H+ (0+) transfer from the CN group to the phenyl ring in which HID exchange occurs. The efficiency of the CN-to-ring H+ (D+) transfer increases in the order para < meta < orrho position. Evidence for incomplete HID atom randomization in Cj;XsCNX+ prior to XCN loss has been obtained. Both processes, CN-toring HID exchange and HID exchange at the phenyl ring, are affected by the internal energy of the Cj;XsCNX+ ions. The results have been interpreted in terms of the internal energy distribution of the ions fragmenting within the metastable time window. Collision-induced dissociation of Cj;XsCNX+ causes the energy-emiched ions to decompose by direct bond cleavage into C 6X;-+ XNC. (J Am Soc Mass Spectrom 1990, 1, 225-232) Address reprint requests to Professor N. M. M. Nibbering,

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Section: Methodsmentioning

confidence: 99%

Site of protonation of benzonitrile hydrogen interchange in the protonated species

Wincel

Fokkens

Nibbering

1990

J. Am. Soc. Mass Spectrom.

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“…Removal of the nitro group from labelled 4‐nitrophenol is typically accomplished by reduction to 4‐aminophenol, followed by diazotisation and removal of the diazonium substituent, either by reduction with hypophosphorous acid64 or by decomposition using zinc oxide in methanol (Scheme ) 3. [1‐ 14 C]Anisole has been prepared by essentially the same approach (Scheme ) 61, 65.…”

Section: Condensation Of Acetone With Nitromalonaldehydementioning

confidence: 99%

Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Gregson

Herbert

Row

2011

Labelled Comp Radiopharmac

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A variety of methods for the preparation of selectively mono-, di-or tri-labelled arenes are reviewed. The review concentrates on those for which the application to labelled synthesis has been demonstrated. Further methods, the application of which to labelled synthesis appears viable but which have not been reduced to practise, are included also. The available methods provide a range of substitution patterns.

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“…, 1979a). For the assistance of the halogen atom in the hydrogen transfer a previous study was invoked on the enol‐keto isomerization of the $[{\rm M} - {\rm C}_2 {\rm H}_4 ]^{ \bullet + }$ ion from o ‐hydroxybutyrophenone which was possible by virtue of the hydroxyl group in the ortho ‐position acting like a catalyst (Molenaar‐Langeveld et al, 1978). Of course, the study of the metastably decomposing ${\rm C}_6 {\rm H}_6 {\rm O}^{ \bullet + }$ ions from the molecular ions of 2‐phenoxyethyl halides (Russell et al .…”

Section: The Years Of Double Focusing Sector Mass Spectrometry Untmentioning

confidence: 99%

Four decades of joy in mass spectrometry

Nibbering

2006

Mass Spectrometry Reviews

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Tremendous developments in mass spectrometry have taken place in the last 40 years. This holds for both the science and the instrumental revolutions in this field. In chemistry the research was heavily focused on organic molecules that upon electron ionization fragmented via complex mechanistic pathways as shown by isotopic labeling experiments. These studies, including ion structure determinations, were performed with use of double focusing mass spectrometers of both conventional and reversed geometry, and equipped with various types of metastable ion scanning and collision-induced dissociation techniques developed by physical and analytical chemists. Time-resolved mass spectrometry by use of the field ionization kinetics method, developed by physical chemists, was another powerful way to unravel details of unimolecular gas phase ion dissociations. Then the development of new ionization methods, such as desorption chemical ionization, field desorption, and fast atom bombardment permitted not only to analyze unvolatile, thermally labile and higher molecular weight compounds, but also to study their chemical behavior in the gas phase, initially with use of double focusing instruments and later on with multisector and hybrid mass spectrometers. These ionization methods also enabled to study organometallic compounds and increasingly the field of medium-sized to large biomolecules, the latter being exploded in the last decade by the development of electrospray- and matrix-assisted laser desorption ionization/time-of-flight mass spectrometry. Another area of research concerned the bimolecular chemistry of organic ions with organic molecules in the gas phase. Initially this was performed with use of among others drift-cell ion cyclotron resonance spectroscopy, that later on was replaced by the developed method of ion trapping and Fourier transform ion cyclotron resonance. Combination of the latter with the afore-mentioned ionization methods has shifted also in this case the research on organic molecules to organometallic/inorganic systems, and predominantly to biomolecules in the last decade. This invited review will describe the research efforts made by the author's group over the last 40 years together with some personal experiences during his career.

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On the apparent ketonization of the [MC₂H₄]⁺ ion from o‐hydroxybutyrophenone

Cited by 12 publications

References 16 publications

Site of protonation of benzonitrile hydrogen interchange in the protonated species

Site of protonation of benzonitrile hydrogen interchange in the protonated species

Synthetic approaches to regiospecifically mono‐ and dilabelled arenes

Four decades of joy in mass spectrometry

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